Synthesis of Chiral AziridinesTechnology #ua16-006
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- Jon Njardarson Professor, Chemistry & Biochemistry
- Isaac Chogii Graduate Assistant, Chemistry & Biochemistry
- Managed By
- Paul Eynott Sr. Licensing Manager (520) 621-2878
Title: One Pot Synthesis of Aziridine
Invention: The invention describes a way to produce chiral aziridine compounds in a one-pot reaction with no metal catalysts. This can offer a significantly reduced cost of production to manufacturers that utilize aziridine.
Background: Existing aziridine synthetic routes can seldom be done in a one step pathway. Furthermore, many syntheses require the uses of metal catalysts to achieve workable yield and still produce potential secondary products that are irrelevant to the use cases at hand.
The synthesis can be applied to creating biofoul resistant coatings for medical devices
Hardening agent for a variety of compounds
One pot synthetic reaction makes creating the compound relatively simple and cuts out costs that would have been associated with extra steps.
No metal components will also reduce costs from standard aziridine synthesis
Chiral output allows selective compounds to be developed and reduces waste and secondary products
Ilardi, E. a., & Njardarson, J. T. (2013). Ring expansions of vinyloxiranes, -thiiranes, and -aziridines: Synthetic approaches, challenges, and catalytic success stories. Journal of Organic Chemistry, 78(19), 9533–9540. http://doi.org/10.1021/jo401776s
Rogers, E., Araki, H., Batory, L. a., McInnis, C. E., & Njardarson, J. T. (2007). Highly selective copper-catalyzed ring expansion of vinyl thiiranes: Application to synthesis of biotin and the heterocyclic core of plavix. Journal of the American Chemical Society, 129(10), 2768–2769. http://doi.org/10.1021/ja069059h
J. T. Njardarson, Catalytic ring expansion adventures. Synlett 24, 787–803 (2013). CrossRefWeb of ScienceGoogle Scholar
Name: Paul Eynott
Technology ID: UA16-006
Inventors: Jon Njardarson and Isaac Chogii